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Compare 25 B&B in Westchester with updated reviews, rates, and availability.

The Villa Toscana
Lounge
The Villa Toscana
2.5 star property
7.8 out of 10, Good, (476)
"Absolutely delighted indeed 🙂 So we’d been traveling for a few days as jenn and I had planned. As all new couples experience we were tired, cranky, needed out of the car with each other. I looked to see how close i could get to Wrigley Field a night earlier than I had booked us months in advance. Boom you had me at “Adults Only” and then my love of “old beautiful houses” “warm friendly feeling” “positive vibes” “positive energy” was satisfied at first glimpse of available room. I booked it....
The price is AED 251
AED 442 total
includes taxes & fees
23 Sep - 24 Sep
The Villa Toscana
Old Chicago Inn
Property entrance
Old Chicago Inn
2.0 star property
7.4 out of 10, Good, (751)
"Great location. Close to parking garage and train station. Clean room. Adequate breakfast. We stayed in the Wrigleyville - Lakeview area for a concert at the Vic. Was perfect location for the weekend."
Old Chicago Inn
House 5863 - Chicago Bed and Breakfast
Exterior
House 5863 - Chicago Bed and Breakfast
3.5 star property
9.0 out of 10, Wonderful, (466)
"Had a nice stay. We had a private bath that was down the hall from our room. Everything was clean. Check in was smooth- we communicated through text and that worked well. "
The price is AED 523
AED 824 total
includes taxes & fees
23 Sep - 24 Sep
House 5863 - Chicago Bed and Breakfast
Ray's Bucktown B&B
Front of property
Ray's Bucktown B&B
3.5 star property
9.8 out of 10, Exceptional, (319)
"Beautiful and eclectic place. I don’t know who dusts everything but they do a great job. Everything spotless and the staff were wonderful. Will be back!"
The price is AED 718
AED 810 total
includes taxes & fees
6 Oct - 7 Oct
Ray's Bucktown B&B
The Sono Chicago
Room
The Sono Chicago
3.5 star property
10.0 out of 10, Exceptional, (429)
"Our first time at a true B & B. I cannot express how much we enjoyed our time at Sono! The friendliness & especially HELPFULNESS of Adie was terrific! We really enjoyed our time in the morning during breakfast with the other guests. We ARE coming back next time we are in Chicago!"
The price is AED 630
AED 740 total
includes taxes & fees
23 Sep - 24 Sep
The Sono Chicago
The Publishing House B&B
Fireplace
The Publishing House B&B
3.5 star property
9.8 out of 10, Exceptional, (157)
"A beautiful B&B in a stunning part of Chicago. So many great restaurants close by and an easy walk to the train. Very accessible to the city. Worth a stay. "
The price is AED 964
AED 1,103 total
includes taxes & fees
14 Oct - 15 Oct
The Publishing House B&B
Wicker Park Inn
Room
Wicker Park Inn
3.5 star property
9.0 out of 10, Wonderful, (235)
"Very nice option if you want to stay outside of downtown but still in the city. Room was nice and clean, would stay again."
The price is AED 922
AED 1,082 total
includes taxes & fees
29 Sep - 30 Sep
Wicker Park Inn
Harvey House Bed & Breakfast
Interior
Harvey House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (100)
"Great location, restful accommodation with lots of beautiful touches. Very welcoming host with excellent communication. "
The price is AED 962
AED 1,068 total
includes taxes & fees
25 Sep - 26 Sep
Harvey House Bed & Breakfast
Villa D' Citta
Front of property
Villa D' Citta
3.5 star property
9.4 out of 10, Exceptional, (92)
"Edith was amazing! She greeted us each morning with coffee, breakfast, and a smile😊 Except the last morning, a woman that introduced herself as the Asst Manager came in while we were eating and complained about the new coffee maker and was pretty unpleasant, but everything and everyone else was excellent!! "
The price is AED 756
AED 888 total
includes taxes & fees
15 Oct - 16 Oct
Villa D' Citta
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Dining Room
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
9.8 out of 10, Exceptional, (130)
"We were thrilled with the little neighborhood and options for food, drinks and shopping. Super easy to hop on bus to and from Wrigley!"
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Villa Dubois Guest Room 6
A cozy bedroom with a patterned wallpaper wall, a large mirror, a queen size bed with grey linens, a bedside table with a lamp and towels, and a window with white curtains.
Villa Dubois Guest Room 6
The price is AED 397
AED 740 total
includes taxes & fees
23 Sep - 24 Sep
Villa Dubois Guest Room 6
Villa Dubois Guest House Room 5
A cozy and modern bedroom with brownish paper wall, a comfortable queen size bed, a large window with natural light, and stylish artwork.
Villa Dubois Guest House Room 5
The price is AED 397
AED 740 total
includes taxes & fees
23 Sep - 24 Sep
Villa Dubois Guest House Room 5
Villa Dubois Guest House Room 2
A simply furnished room with a plush armchair, a wooden table with and a framed painting on a blue ash paper wall.
Villa Dubois Guest House Room 2
The price is AED 397
AED 740 total
includes taxes & fees
23 Sep - 24 Sep
Villa Dubois Guest House Room 2
Dubois Guest House Room 101
Cozy bedroom with a patterned wallpaper wall, a queen sized bed with grey linens, a ceiling fan, a vanity area with a mirror and chair,and a window with white curtains.
Dubois Guest House Room 101
The price is AED 397
AED 740 total
includes taxes & fees
23 Sep - 24 Sep
Dubois Guest House Room 101
Dubois Guest House Room 201
Cozy bedroom with a patterned wallpaper wall, a large mirror, a queen size bed with grey linens, a bedside table with a lamp and towels, and a window with white curtains.
Dubois Guest House Room 201
9.0 out of 10, Wonderful, (2)
The price is AED 397
AED 740 total
includes taxes & fees
23 Sep - 24 Sep
Dubois Guest House Room 201
Room in Town house Rogers Park
Living area
Room in Town house Rogers Park
Room in Town house Rogers Park
Dubois Guest House Room 202
Cozy bedroom with a patterned wallpaper wall, a large mirror, a queen size bed with grey linens, a bedside table with a lamp and towels, and a window with white curtains.
Dubois Guest House Room 202
The price is AED 397
AED 740 total
includes taxes & fees
23 Sep - 24 Sep
Dubois Guest House Room 202
Villa Dubois Guest House Room 1
King size bed, grey with blue wall paper design
Villa Dubois Guest House Room 1
The price is AED 496
AED 863 total
includes taxes & fees
25 Sep - 26 Sep
Villa Dubois Guest House Room 1
Villa Dubois Guest House Room 4
A cozy and stylish bedroom with a comfortable bed, a patterned armchair, and a unique wall decoration.
Villa Dubois Guest House Room 4
The price is AED 397
AED 740 total
includes taxes & fees
23 Sep - 24 Sep
Villa Dubois Guest House Room 4
Dubois Guest House Room 203
Close view of bedroom with a patterned accent wall, a queen size bed with grey linens, a ceiling fan, a vanity area with a mirror and chair, and a window with white curtains.
Dubois Guest House Room 203
The price is AED 496
AED 874 total
includes taxes & fees
23 Sep - 24 Sep
Dubois Guest House Room 203
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Westchester

Sentral Michigan Avenue
Garden
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (543)
"Wonderful place "
The price is AED 559
AED 764 total
includes taxes & fees
30 Sep - 1 Oct
Sentral Michigan Avenue
Sonder South Wabash
Interior
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (370)
"Great place to stay in the South Loop area. Super nice. Super clean. Super quiet."
The price is AED 728
AED 855 total
includes taxes & fees
21 Oct - 22 Oct
Sonder South Wabash
Sonder Market Hall
Living area
Sonder Market Hall
3.5 star property
8.8 out of 10, Excellent, (160)
"The apartment was very nice and modern with great amenities. The walls, ceilings and/or floors were not very sound proof. If that could be improved i woule have given 5 atard across the board."
The price is AED 540
AED 634 total
includes taxes & fees
30 Sep - 1 Oct
Sonder Market Hall
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Searching for B&Bs in Westchester?
Whether you’re on a family vacation and want a small, cozy place to stay, or you’re traveling solo and hoping to meet fellow tourists, B&Bs can be a great choice for many travelers. If you’re interested in discovering some top attractions, Wrigley Field and Millennium Park are worth a stop.
Why consider B&Bs instead of traditional hotels?
With attentive service, opportunities to mingle with other guests, and of course a full breakfast to start the day, B&Bs offer a truly one-of-a-kind environment.
What are the best B&Bs in Westchester?
Here are some well-liked B&Bs in the area: The Villa Toscana: 9 rooms. 13.6 mi (21.9 km) from the heart of Westchester.Old Chicago Inn: 10 rooms. 13.2 mi (21.3 km) from the downtown core. Enjoy the free full breakfast and fireplace in the lobby. Ray’s Bucktown B&B: 11 rooms. Situated 11.3 mi (18.2 km) from the heart of Westchester. Enjoy the free cooked breakfast and rooftop terrace. House 5863 - Chicago Bed and Breakfast: 7 rooms. 14.7 mi (23.6 km) from the heart of downtown. Enjoy the designer toiletries and private yard. The Sono Chicago: 7 rooms. Located 13 mi (20.9 km) from the core of Westchester. Enjoy the rooftop terrace and fireplace in the lobby.
What's the best time of year to book my B&B in Westchester?
When you’re planning your getaway to Westchester, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Westchester are January, November, February, and December, with each month seeing an average of 5 inches of snowfall.
What is there to do in Westchester?
Travelers enjoy Westchester for its restaurants and shopping. You might also consider a trip to sites like Wrigley Field or Millennium Park if you have time to see more of the area.
How can I get to and around Westchester?
You can map out your trip in and around Westchester ahead of time with these transportation options. Fly into Chicago Midway Airport (MDW), which is located 8.4 mi (13.4 km) away from the heart of the city. Otherwise, you can search for flights to Chicago O’Hare Intl. Airport (ORD), which is 8.9 mi (14.3 km) away. If you’d like to explore around the area, you may want a rental car for your journey.